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Barbituric acid-cyclopentene spiro compound and preparation method thereof

A technology of spiro compound and barbiturate is applied in the field of organic compound synthesis to achieve high stereoselectivity and enantioselectivity, increase diversity and expand applicability

Active Publication Date: 2018-12-04
CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although there have been many reports on the synthesis of barbituric acid spiro compounds, there are few reports on the synthesis of barbituric acid five-membered spiro compounds.

Method used

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  • Barbituric acid-cyclopentene spiro compound and preparation method thereof
  • Barbituric acid-cyclopentene spiro compound and preparation method thereof
  • Barbituric acid-cyclopentene spiro compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031]

[0032]Put 0.0244g (0.100mmol) of compound 1a, 0.0350g (0.120mmol) of compound 2a and 3mL of 1,2-dichloroethane into a dry 15mL Shrek tube, add 0.020mmol of methyl diphenylphosphine and mix well Carry out a cycloaddition reaction. In the reaction system, the molar ratio of compound 1a to compound 2a is 1:1.2, methyldiphenylphosphine accounts for 20% of the molar percentage of compound 1a, stirred at 40°C for 24 hours, and concentrated through the column with a rotary evaporator (Ethyl acetate:petroleum ether=1:10, v / v), 23.4 mg of product 3aa was obtained, with a yield of 56%.

Embodiment 2

[0034]

[0035] Put 0.0244g (0.100mmol) of compound 1a, 0.0350g (0.120mmol) of compound 2a and 3mL of toluene into a dry 15mL Shrek tube, add 0.020mmol of methyl diphenylphosphine and mix well for cycloaddition reaction. In the reaction system, the molar ratio of compound 1a to compound 2a is 1:1.2, methyldiphenylphosphine accounts for 20% of the molar percentage of compound 1a, stirred at 40°C for 24 hours, and concentrated through the column with a rotary evaporator (Ethyl acetate:petroleum ether=1:10, v / v), 36.8 mg of product 3aa was obtained, with a yield of 89%.

[0036] It can be seen that the effect is very excellent when selecting toluene as the solvent.

Embodiment 3

[0038]

[0039] Put 0.0244g (0.100mmol) of compound 1a, 0.0350g (0.120mmol) of compound 2a and 3mL of toluene into a dry 15mL Shrek tube, add 0.020mmol of dimethylphenylphosphine and mix well for cycloaddition reaction. In this reaction system, the molar ratio of compound 1a to compound 2a is 1:1.2, dimethylphenylphosphine accounts for 20% of the molar percentage of compound 1a, stirred at 40°C for 24 hours, concentrated through the column with a rotary evaporator (Ethyl acetate:petroleum ether=1:10, v / v), 31.5 mg of product 3aa was obtained, with a yield of 76%.

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PUM

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Abstract

The invention relates to barbituric acid-cyclopentene spiro-compounds and a preparation method thereof. The preparation method comprises the following steps: in a dry Schlenk tube, uniformly mixing compounds 1 and Morita-Baylis-Hillman adducts 2 in a solvent, adding an organic phosphine catalyst, stirring, and carrying out cycloaddition reaction to obtain the spiro-compounds 3; and in a dry Schlenk tube, uniformly mixing compounds 1 and Morita-Baylis-Hillman adducts 2 in a solvent, adding a chiral organic phosphine catalyst and additives, stirring, and carrying out cycloaddition reaction to obtain the chiral spiro-compounds 4. The invention provides a simple and feasible novel method for synthesizing pyranobarbituric acid spiro-compounds. The method adopts the cycloaddition reaction mode, and belongs to atomic economical reaction. By using the organic phosphine as the catalyst instead of the transition metal catalyst, no heavy metal pollution can exist in the product. The synthetic compounds are not reported in the documents, and are all new compounds.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, and in particular relates to a class of barbituric acid-cyclopentene spiro compounds and a preparation method thereof. Background technique [0002] Barbituric acid spiro compounds are also a class of biologically active molecules, which have antispasmodic and enzyme inhibitors (J.Chem.Soc., Perkin Trans.1 1990, 3137-3144.; Pharm.Res.1995 , 12, 1240-1243.; J. Org. Chem. 2002, 67, 1302-1307.; Bioorg. Med. Chem. Lett. 2005, 15, 1101-1106.). Barbituric acid and its various derivatives are structural units of natural products and drugs with important biological activities. They have various biological activities such as sedation, anti-convulsion, anti-malarial, anti-virus and potential anti-cancer. Some compounds have been put into To clinical application and achieved good results (Chem.Commun.2000, 65, 1082., J.Med.Chem.2001, 44, 2544.; J.OrgChem.2003, 68, 4684.; Clin.Cancer Res....

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/70
CPCC07D239/70
Inventor 郭红超刘洋王博
Owner CHINA AGRI UNIV
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